Potassium Carbonate → (5R)-3-{3-Fluoro-4-[2-methyl-6-(4-methyl-1H-1,2,3-triazol-1-yl)pyrid-3-yl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

HRID 1782095Notes

Reaction equation

HRID 1782095 reaction equation
Br[C:2]1[C:3]([CH3:14])=[N:4][C:5]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]2)=[CH:6][CH:7]=1.[F:15][C:16]1[CH:17]=[C:18]([N:31]2[CH2:35][C@H:34]([CH2:36][N:37]3[CH:41]=[CH:40][N:39]=[N:38]3)[O:33][C:32]2=[O:42])[CH:19]=[CH:20][C:21]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:15][C:16]1[CH:17]=[C:18]([N:31]2[CH2:35][C@H:34]([CH2:36][N:37]3[CH:41]=[CH:40][N:39]=[N:38]3)[O:33][C:32]2=[O:42])[CH:19]=[CH:20][C:21]=1[C:2]1[C:3]([CH3:14])=[N:4][C:5]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 23626595(5R)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-oneHCID 575882863-Bromo-2-methyl-6-(4-methyl-1H-1,2,3-triazol-1-yl)pyridine

Product 1

HCID 57588298(5R)-3-{3-Fluoro-4-[2-methyl-6-(4-methyl-1H-1,2,3-triazol-1-yl)pyrid-3-yl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 3

HCID 178420553HCID 178420553, compoundCatalystHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

3-Bromo-2-methyl-6-(4-methyl-1H-1,2,3-triazol-1-yl)pyridine (196 mg, 0.773 mmol), (5R)-3-[3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (300 mg, 0.773 mmol), potassium carbonate (320 mg, 2.31 mmol), and tetrakis(triphenylphosphino) palladium(0) (89 mg, 0.077 mmol) were combined and suspended in DMF (3 ml) and water (0.3 ml). The mixture was heated at 80° C. for 2 hours, then diluted with water to 7 ml. The solids were collected, rinsed with water and resuspended in warm DMSO (3 ml). The suspension was diluted with dichloromethane (5 ml) and ether (4 ml). The solid was collected, rinsed with ether and methanol, and dried in vacuo to give the pure product as a white solid, 110 mg.

Workup

  1. customThe solids were collected
  2. washrinsed with water
  3. additionThe suspension was diluted with dichloromethane (5 ml) and ether (4 ml)
  4. customThe solid was collected
  5. washrinsed with ether and methanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-47e842f87cde4cdebc9744f952354621
Source dataset
uspto-grants-2009_03
Patent number
US07498350B2

Reaction notes

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